Dennis Hopper, Paul Newman, Marvin Gaye: Are you ready to join the ranks of the most legendary denim-shirt men? Those fellas understood that the right denim shirt won’t just make you look rugged and handsome and all kinds of confident—it’ll also solve virtually any wardrobe-related dilemma that comes your way. For instance:
- Got your sixth wedding of the fall coming up and fully tapped out of dress-shirt-and-tie combos you like? Throw a denim shirt into the mix, and your tired flannel suit’s suddenly supercharged with rugged sex appeal.
- Copped some wild patterned pants on a whim and now concerned you can’t pull them off? A classically handsome denim shirt will lock ’em down and balance out the swerviness.
- Want to look good on the weekend but too damn lazy to really think about it? Denim shirt, white T-shirt, black jeans, can’t lose.
- Giving an important presentation at work when your trousers embarrassingly split right down the seat? Okay, well, a denim shirt probably can’t help you there. That’s when you ask yourself question number two: What’s my tailor’s phone number again?
So, yeah: Denim shirts are useful. Like, having-a-sibling-who’s-a-contractor useful. They’re an American classic and a menswear staple that deserves a space (or two) in your closet. And the two most useful kinds of denim shirts are button-down and Western, which you’ll probably want in a medium-to-light wash for maximum versatility. Here are 22 of the best men’s denim shirts that’ll help to really tie your fits together.
The Gold Standard Denim Shirt
You knew it was coming. More than 160 years into their run, it’s hard to picture anybody coming for Levi’s’ crown. The first name in jeans still makes one of the best Western shirts you’ll find anywhere: The fit is just right for layering, the details are on point, and the fabric of this particular version is made sustainably, using way less water than regular denim. Add in a super-reasonable $70 price tag, and you’ve got yourself a wardrobe staple for the ages.
The OG Western Shirt
You know those pearly snap buttons on the front of every yeehaw-ready Western shirt you’ve ever worn? You can thank Rockmount Ranch Wear for them. The Denver outfitter’s original snap-front long-sleeves have been donned by everyone from Bob Dylan (during his Presidential Medal of Freedom ceremony, no less) to the entire cast of Brokeback Mountain. The label makes their fair share of frill-free denim numbers, too, but ornate embroidery is a part of Rockmount’s essential DNA. So if you’re gonna go for it, why not really go for it?
The A-List Denim Shirt
Ever see paparazzi snaps of dudes like Brad Pitt or Ryan Gosling and wonder how their seemingly regular clothes always look so damn crisp and impeccably just-so? Well, for starters, they’re much, much better-looking than you. That tends to help. But the good genetics also extend to their wardrobes: Guys like that can afford shirts like this one, exactingly engineered by Italian tailoring god Brunello Cucinelli to make anyone—even mere mortals like you—look and feel like a matinee idol. The chambray is the ideal weight—light enough to be comfortable, thick enough for some structure—and the cut is trim and sharp like a dress shirt, which means you can wear it tucked in with a suit, or rolled up and rumpled with chinos, and it’ll never not radiate perfectly imperfect movie-star cool.
The Office-Ready Denim Shirt
Sid Mashburn’s crisp chambray shirt is the best way to bring all the utility and character of denim with you to work and on dressy nights out. Fresh off the ironing board, it’ll clean up well with a suit and tie or a sport coat and jeans. But this shirt truly shines on a Sunday morning, left a little rumpled with a few buttons undone—you’ll feel like a wise, old Italian man sipping an espresso and smoking a cigar on the streets of Napoli. What more could you ask for?
The Absolute Grail Denim Shirt
Kapital’s boro western shirt is an absolute work of art. It comes courtesy of the acclaimed denim label’s Kapital Kountry sub-label, famed for its meticulous use of Japanese boro fabrics, over-the-top distressing, and obsessive handiwork. It requires and dozens dozens of hours to hand-stitch this achieve this level of detail, a perfect mashup of traditional Japanese technique and dyed-in-the-wool Americana style.
The Best Relaxed Denim Shirt
Remember Dennis Quaid in The Parent Trap? The perfectly louche way his shirts hung? How beautifully washed-out the denim was? Based on this shirt, we’re guessing everyone’s favorite Napa Valley vintner was all over J.Crew’s moodboard this season. It hits all the right notes: all-cotton denim; a natural, lived-in wash; handsome white buttons; comfortable, roomy fit. Wear it with a thick thermal shirt, or layer it over a light sweater like you would an overshirt. Don’t be afraid to go full Canadian tuxedo, or pair it with a white T-shirt and wide-leg twill chinos to relive that oh-so-good ’90s J.Crew catalog vibe.
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